Diisopropylethylamine → HCID 24876089, compound

HRID 1851832Notes

Reaction equation

HRID 1851832 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]1([CH2:16][O:17][C:18]([NH:20][C:21]2([C:27]([NH:29][C@H:30]([CH2:34][OH:35])[CH:31]([CH3:33])[CH3:32])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.C(Cl)Cl>[C:10]1([CH2:16][O:17][C:18]([NH:20][C:21]2([C:27]([NH:29][C@H:30]([CH:34]=[O:35])[CH:31]([CH3:33])[CH3:32])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 24875999N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol

Product 1

HCID 24876089HCID 24876089, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, 1.22 g (9.44 mmol) of N,N-diisopropylethylamine was added dropwise to a solution of 1.50 g (9.44 mmol) of sulfur trioxide-pyridine complex in 10 ml of anhydrous dimethyl sulfoxide and 5 ml of anhydrous methylene chloride under ice-cooling, the mixture was stirred for 15 minutes. Further, a solution of 570 mg (1.57 mmol) of N-[[1-[[(phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol in 3 ml of anhydrous dimethyl sulfoxide was added to the reaction solution under ice-cooling, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured into ice water and extracted with ethyl acetate twice. The organic layer was washed with a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution, and then saturated brine, and after it was dried with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the residue, and the mixture was stirred at room temperature for 18 hours. The obtained crystal was collected by filtration to give 435 mg (77%) of the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 2 hours
  4. extractionextracted with ethyl acetate twice
  5. washThe organic layer was washed with a 10% aqueous citric acid solution
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution, and then saturated brine, and after it was dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. addition20 ml of diisopropyl ether was added to the residue
  9. stirringthe mixture was stirred at room temperature for 18 hours
  10. filtrationThe obtained crystal was collected by filtration

Sources & evidence

ORD record
ord-4c4a5089f18f4b278b28323f764240f1
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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